The 1960s

The 1960s are presented as a decade in which private life and public danger move in opposite directions. Frank Sheeran begins to leave behind some of his street hustles as he builds a new family life, while James R. Hoffa faces growing legal pressure and a deepening conflict with Robert F. Kennedy. The book’s later disputes over what Sheeran confessed, and what could be independently verified, make the decade not only a period of events but also a contested history reconstructed years afterward.

A New Marriage and a Retreat from Hustling

Around this period, Sheeran began dating Irene whenever he was in Philadelphia. They fell in love, and she wanted a family. Sheeran explained the relationship to Mary, who agreed to a divorce; he and Irene married soon afterward, and their daughter Connie was born the next year. The sequence marks a change in the shape of Sheeran’s life: a new household followed quickly by a new child.

Sheeran described the marriage as a reason to step back from the work that had filled his earlier days. He gave up selling the football lottery after several arrests and fines, and no longer needed the downtown hustling associated with Joey McGreal. Even his activity within the Teamsters culture slowed. He stopped making trips across the bridge from Detroit to Windsor with Bill Isabel and Sam Portwine, a place he remembered as lively before the United States opened up. Rather than continuing to participate in that world, he became a spectator.

The retreat did not mean that Sheeran was without income. During his marriage to Irene, he had steady money from more than one Teamsters job, a practice that was later outlawed. The book contrasts the relative financial security of Connie’s childhood with the more limited means available to Sheeran’s older daughters. His account of the decade therefore joins a personal change in direction to a continuing dependence on union work.

Hoffa and the Kennedy Conflict

For Hoffa, the decade brought a mounting sense that the political balance had turned against him. Sheeran recounts that Hoffa regarded John F. Kennedy’s election as bad for him and saw the appointment of Robert F. Kennedy as attorney general as a particularly bitter blow from the Kennedy family. Hoffa expected the legal action to worsen. His hostility also extended to political allies he believed had been taken in by glamour and celebrity; Sheeran recalls him blaming Chicago associates for supporting the Kennedy campaign and criticizing their judgment.

That hostility was more than political rhetoric in the book’s account. At a private Washington dinner, President John F. Kennedy told journalist Ben Bradlee that Hoffa was plotting to kill his brother. Bradlee’s personal journal reportedly recorded that the President was serious. When Bradlee approached Robert F. Kennedy, however, the attorney general urged him not to publish: publicizing the threat could frighten potential witnesses in the organized-crime cases under his supervision. Bradlee withheld the story. The episode places the alleged threat at the intersection of presidential concern, prosecutorial strategy, and the effort to protect witnesses.

The conflict also appears in a more intimate register. Sheeran recounts Hoffa’s resentment of Robert F. Kennedy, while Bill Isabel later told him that Hoffa was never the same after Kennedy crossed his path. Sheeran compares their mutual pursuit to a white-whale chase: each man was both pursuer and pursued. The image captures a relationship in which neither side could be reduced simply to hunter or quarry.

The Test Fleet Prosecution

A concrete legal confrontation arrived with the Test Fleet case. The trial was scheduled for October 22, 1962, and concerned alleged violations of the Taft–Hartley Act. The charges involved a car-hauling company placed in the names of the wives of Hoffa and the late Owen Bert Brennan. The activity had ended five years earlier and had already been investigated by the McClellan Committee and the Justice Department. Prosecutors argued that Test Fleet formed part of a long-term arrangement to pay Hoffa after he had settled a strike favorably for the employer that later did business with the company.

The case carried a second risk beyond its underlying charge. The Test Fleet allegation was a misdemeanor, but suspected jury tampering in Hoffa’s earlier trials had not produced a conviction. If attempts to influence jurors were established, the stakes could rise to a felony. The Get Hoffa Squad placed Edward Grady Partin in Hoffa’s entourage in Nashville, where Partin served as a guard outside Hoffa’s suite. Walter Sheridan later admitted that Partin was given a recording device for calls with Hoffa and was instructed to watch for attempts to bribe jurors. The arrangement made the trial both a prosecution of Hoffa and an opportunity to gather evidence about possible interference with the jury.

Confession, Documentation, and the Later Record

The book situates its account of the decade within a longer dispute over Sheeran’s willingness to confess. In 1978, a controversy arose over whether he had confessed by telephone to Steven Brill, possibly while intoxicated. The FBI believed Sheeran had confessed and pressed Brill for a recording. Dan Moldea later wrote that Brill had told him over breakfast that he possessed a recorded confession; Brill publicly denied the claim in The New York Times. During the later interviews for the book, the effort was to preserve Sheeran’s rights so that his statements would not amount to a confession admissible in court. Sheeran read and approved each chapter and then the complete manuscript, a process that makes his participation in the account explicit without resolving the contested status of his claims.

Other later revelations further complicate the record. A letter presented in connection with Hoffa proved to be a forgery: its paper dated from 1994 rather than 1974, and its signature had been traced over a faint photocopy. Sheeran admitted that the letter had given him a way out if the pressure became too great. The publisher canceled the book despite the editor’s belief in Sheeran’s account of Hoffa’s killing. The episode demonstrates why the narrative cannot be treated as a seamless confession: Sheeran could supply material that appeared to support his story while also maintaining an escape route from it.

Investigative records and forensic tests later added evidence without closing the question. In 2002, after years of pressure and a failed lawsuit by Hoffa’s children seeking the FBI file, the bureau released a censored 349-page case summary. The Detroit Free Press reported that names had been removed, witness interviews blacked out, and pages omitted; a separate release of 1,400 pages from the bureau’s much larger file suggested that its most significant leads had run out in 1978. Before the book’s first edition appeared, Fox News investigators found eight tiny traces of blood in a trail from the vestibule down the hallway toward the kitchen of the house where Sheeran said he shot Hoffa. Testing announced in 2005 identified human male blood but found that its DNA did not match Hoffa’s. The result neither corroborated the confession nor refuted it, leaving the book’s account of the 1960s—and the violence it says culminated later—suspended between recollection, disputed documents, and incomplete physical evidence.